The development of diastereoselective and regioselective oxidative galloyl coupling transformations will be explored within the context of a strategy for ellagitannin total chemical synthesis. Specifically, concise and stereorational syntheses of the increasingly structurally complex targets corilagin, pedunculagin, coriariin A, and agrimoniin will be pursued. Successful execution of this strategy will impact on contemporary hypotheses of ellagitannin biosynthesis, both by demonstrating the feasibility of current models and by illuminating subtle (stereo) chemical exigencies. Synthesis studies will provide substrates for protein recognition, binding and chromatography experiments with natural gallotannins, and ellagitannins and rationally designed, simplified analogs. In addition, an in vitro combinatorial peptide library approach will be utilized to screen for amino acid sequences which are particularly effective at recognizing ellagitannins at therapeutically useful levels. Taken together, these biological investigations will contribute to a molecular-level understanding of the functional, structural, and stereochemical requirements for protein recognition which presumably, undergrid the vast commercially and therapeutically important area of protein/tannin interactions.